2-Methyl-4-(3-nitro-phenyl)-6-[2-(4-phenyl-piperazin-1-yl)-ethyl]-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester | 75956-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-Methyl-4-(3-nitro-phenyl)-6-[2-(4-phenyl-piperazin-1-yl)-ethyl]-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester
• 英文别名: diethyl 2-methyl-4-(3-nitrophenyl)-6-[2-(4-phenylpiperazin-1-yl)ethyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 75956-07-9
• 化学式: C₃₀H₃₆N₄O₆
• 分子量: 548.639
• InChiKey: MZXXIMYLBAOHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  114.25
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  间硝苯地平 、 聚合甲醛 、 N-苯基哌嗪 以20%的产率得到
  参考文献：
  名称：

  ARITOMI JIRO; UEDA SHOZO; NISHIMURA HARUKI, CHEM. AND PHARM. BULL., 1980, 28, NO 11, 3163-3171

  摘要：

  DOI：

文献信息

• Mannich reaction of dihydropyridine derivatives I. Reactions with secondary amines.
  作者：JIRO ARITOMI、SHOZO UEDA、HARUKI NISHIMURA

  DOI：10.1248/cpb.28.3163

  日期：——

  Dialkyl 4-aryl-1, 4-dihydro-2, 6-dimethylpyridine-3, 5-dicarboxylates (III) were subjected to the Mannich reaction with excess paraformaldehyde and secondary amine hydrochloride in boiling ethanolic solution. When the compounds III were treated with a 5-to 7-fold molar excess of the aldehyde and amine salt, 2, 6-bis (2-disubstituted aminoethyl)-dihydropyridine derivatives (V) were obtained in good yields. On treatment with a 2- to 3-fold molar excess of the reactants, compounds III were converted to 2-(2-disubstituted aminoethyl)-6-methyldihydropyridine derivatives (IV) and V. When dioxane was used as a solvent with a 6-fold molar excess of the reactants, the tetrakis (dimethylaminomethyl) derivative (VII) was obtained.

  二烷基 4-芳基-1, 4-二氢-2, 6-二甲基吡啶-3, 5-二羧酸酯 (III) 在沸腾的乙醇溶液中与过量的多聚甲醛和二级胺盐酸盐进行曼尼希反应。当化合物 III经5-至7-倍摩尔过量的醛和胺盐处理时，可获得产率良好的 2, 6-双(2-二取代氨基乙基)-二氢吡啶衍生物 (V)。用2-至3-倍摩尔过量的反应物处理时，化合物 III 转化成 2-(2-二取代氨基乙基)-6-甲基二氢吡啶衍生物 (IV) 和 V。当使用二氧六环作为溶剂并采用6-倍摩尔过量的反应物时，得到四(二甲氨基甲基)衍生物 (VII)。